2-Chloro-N-(3-fluorophenyl)-4-(3-nitrophenyl)pyrimidin-5-amine → 4-(3-aminophenyl)-2-chloro-N-(3-fluorophenyl)pyrimidin-5-amine

HRID 1500801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500801
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)[C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[CH:4][N:3]=1.[H][H]>C(O)C.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]([C:6]2[C:5]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 2

HCID 866775212-Chloro-N-(3-fluorophenyl)-4-(3-nitrophenyl)pyrimidin-5-amineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 866775204-(3-aminophenyl)-2-chloro-N-(3-fluorophenyl)pyrimidin-5-amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Chloro-N-(3-fluorophenyl)-4-(3-nitrophenyl)pyrimidin-5-amine (50 mg, 0.145 mmol) was added to the palladium/carbon (10 mg, 0.015 mmol) in ethanol (25 mL) and the applied hydrogen gas at 8 psi for 2 h at rt. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite; the solvent was removed by vacuum; and the crude material was purified by flash chromatography (2% CH3OH/DCM) to yield the title compound (35 mg, 0.145 mmol) as a solid. 1H NMR: (CDCl3, 400 MHz): δ 8.40 (s, 1H), 7.65 (m, 1H), 7.27-7.17 (m, 4H), 7.13-7.09 (m, 2H), 6.77 (m, 1H), 6.68 (m, 1H). ESI-MS: m/z 315.0 [M+H]+.

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite
  3. customthe solvent was removed by vacuum
  4. customand the crude material was purified by flash chromatography (2% CH3OH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-d5e1155fcca64f28b432e3a6f35f39b7
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206176B2

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